Cyrus E. Cheslak

        Associate
        Contact Info
        Cyrus E. Cheslak Cyrus E. Cheslak

        Cyrus is a dedicated, hands-on problem-solver who works closely with clients to help them navigate various employment law matters.

        As a member of Verrill’s Labor and Employment Group, Cyrus assists clients with a variety of employment-related matters, including discrimination and harassment claims, employment litigation, and employee relations. He also supports clients in employment counseling matters, including developing and implementing workplace policies and procedures and advising on compliance with evolving legal obligations.

        Drawing on his strong research and writing skills and background in politics, Cyrus approaches each matter in a thoughtful, methodical, and pragmatic way, tailoring his work to align with each client’s operations and goals.

        During law school, Cyrus was a student attorney for the Cumberland County District Attorney’s Office and Cumberland Legal Aid Clinic, and a judicial expert to the Honorable Kermit V. Lipez of the United States Court of Appeals for the First Circuit. He also served as a teaching assistant for the Legal Research & Writing Program and tutored first-year law students, served as Head Case Note & Comment Editor of the Maine Law Review, and competed on Maine Law’s Trial Competition and Moot Court Teams. After graduating magna cum laude from the University of Maine School of Law, Cyrus clerked for The Honorable Thomas E. Humphrey of the Maine Supreme Judicial Court.

        Prior to law school, Cyrus was an aide to United States Senator Susan M. Collins in Washington D.C., where he worked on a variety of legislative matters including health care, agriculture, and nutrition policy, and managed the office’s administrative operations. Cyrus maintains a strong interest in the public policy space.

        Cyrus now lives in Portland with his family and two dogs, where he enjoys hosting backyard barbeques, visiting Maine’s famed breweries, and hiking and exploring Maine’s natural beauty with his kids.

        Services/Industries

        Education

        • University of Maine School of Law (J.D., magna cum laude)
          • Head Case Note & Comment Editor – Maine Law Review
        • Franklin & Marshall College (B.A.)

        Public Service

        • Maine State Bar Association Leadership Academy

        Bar Admissions

        • Maine
        • Massachusetts

        Court and Other Admissions

        • U.S. District Court for the District of Maine

        Memberships

        • Maine State Bar Association
        • Tri-State Defense Lawyers Association
        • Cumberland Bar Association

        Honors

        • Best Brief, Craven Moot Court Competition
        • Faculty Significant Achievement Award
        • Named to New England Super Lawyers Rising Stars list under Civil Litigation: Defense

        Learn more about the third-party ratings, rankings, and selection processes used for inclusion.

        Clerkships

        • Maine Supreme Judicial Court, Justice Humphrey
        Events
        When: August 12, 2026 at 11:00am - 12:00pm ET
        Location: Zoom
        When: June 24, 2026 at 11:00am - 12:00pm
        Location: Webinar

        Firm Highlights

        Alerts and Newsletters

        Verrill Secures SJC Victory for Boston Legacy FC in White Stadium Litigation

        Verrill has secured a significant appellate victory for Boston Legacy FC in the litigation challenging the redevelopment of White Stadium in...
        Blog

        Hurry Up and Wait

        This is the third in a series of Verrill blog posts on Maine’s packaging extended producer responsibility (“EPR”) law[1]. In July we reported...
        Media Mentions

        Robert Keach Discusses First Brands Chapter 11 Case in Law360

        Verrill attorney Robert Keach was recently quoted in a Law360 article examining the rejection of First Brands Group's Chapter 11 plan and the...
        Media Mentions

        Cybersecurity and AI Governance: Scott Anderson Featured in Massachusetts Lawyers Weekly

        Verrill Managing Partner Scott Anderson was recently featured in Massachusetts Lawyers Weekly discussing how law firms can build attorney buy-in for...
        Blog

        Section 530A Account Update: ERISA Status of Trump Accounts

        The Department of Labor has issued important guidance addressing whether employer programs that permit contributions to Section 530A accounts (and...
        Press Releases

        97 Verrill Attorneys Recognized by Best Lawyers® 2027, Including Four Named Lawyers of the Year

        AUGUSTA, Maine, BANGOR, Maine, BOSTON, Mass., PORTLAND, Maine, and WESTPORT, Conn., (August 20, 2026) – Verrill is proud to announce that 97...
        Alerts and Newsletters

        SEC’s Proposed “Reg Crypto”: What Founders Need to Know

        Startup founders and emerging-growth companies have a number of options for raising capital under the federal securities laws, including Regulation D...
        Blog

        After 45 Years, the IRS Speaks on DCAP Nondiscrimination Testing – And It’s Good News

        Employers that provide a Dependent Care Assistance Program will be pleased to learn that for the first time in 45 years, the IRS has issued guidance...
        Media Mentions

        U.S. Courts Highlights Annabel Rodriguez’s Journey from Fellow to Mentor

        Verrill attorney Annabel Rodriguez was featured in a recent U.S. Courts article titled “From Fellows to Mentors: Alumni Share Lasting Lessons from...
        Media Mentions

        Robert Keach Discusses Bankruptcy Auction Strategy in Law360

        Verrill attorney Robert Keach spoke with Law360 article examining the complex bankruptcy auction process that resulted in the sale of 23 summer...
        Media Mentions

        Martha Gaythwaite Featured in Portland Press Herald Coverage of Sig Sauer Trial Victory

        Verrill attorney Martha Gaythwaite was highlighted in media coverage of a federal trial in Bangor involving firearm manufacturer Sig Sauer. As...
        Media Mentions

        Law360 Quotes Robert Keach on Senate Bill Affecting Small Business Restructurings

        Verrill attorney Robert Keach was recently quoted in a Law360 article discussing federal legislation that would permanently restore the $7.5 million...